Highly enantioselective synthesis of β-amino alcohols

被引:32
作者
Metro, Thomas-Xavier [1 ]
Appenzeller, Jerome [1 ]
Pardo, Domingo Gomez [1 ]
Cossy, Janine [1 ]
机构
[1] Ecole Super Phys & Chim Ind Ville Paris, Chim Organ Lab, CNRS, F-75231 Paris 05, France
关键词
D O I
10.1021/ol061133d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N,N-Dialkyl-beta-amino alcohols derived from alpha-amino acids can be rearranged enantiospecifically by using TFAA/Et3N/NaOH to give 1,2-amino alcohols with enantiomeric excess up to 99%.
引用
收藏
页码:3509 / 3512
页数:4
相关论文
共 34 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]   Concepts for ligand design in asymmetric catalysis: a study of chiral amino thiol ligands [J].
Anderson, JC ;
Cubbon, R ;
Harding, M ;
James, DS .
TETRAHEDRON-ASYMMETRY, 1998, 9 (19) :3461-3490
[3]   Stereospecific rearrangements during the synthesis of pyrrolidines and related heterocycles from cyclizations of amino alcohols with vinyl sulfones [J].
Back, TG ;
Parvez, M ;
Zhai, HM .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9389-9393
[4]   The synthesis of vicinal amino alcohols [J].
Bergmeier, SC .
TETRAHEDRON, 2000, 56 (17) :2561-2576
[5]  
Bernardi L, 2002, EUR J ORG CHEM, V2002, P2776
[6]  
Betsbrugge JV, 1997, TETRAHEDRON, V53, P9233
[7]   A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone [J].
Brandi, A ;
Cicchi, S ;
Paschetta, V ;
Pardo, DG ;
Cossy, J .
TETRAHEDRON LETTERS, 2002, 43 (51) :9357-9359
[8]   Chiral ferrocenyl amino alcohols as catalysts for the enantioselective borane reduction of ketones [J].
Brunin, T ;
Cabou, J ;
Bastin, S ;
Brocard, J ;
Pélinski, L .
TETRAHEDRON-ASYMMETRY, 2002, 13 (12) :1241-1243
[9]   Calcium trifluoromethanesulfonate-catalysed aminolysis of epoxides [J].
Cepanec, I ;
Litvic, M ;
Mikuldas, H ;
Bartolincic, A ;
Vinkovic, V .
TETRAHEDRON, 2003, 59 (14) :2435-2439
[10]   Chiral oxime ethers in asymmetric synthesis.: Part 7 -: O-(1-phenylbutyl)benzyloxyacetaldoxime, a versatile reagent for the asymmetric synthesis of protected 1,2-aminoalcohols, α-amino acid derivatives, and 2-hydroxymethyl nitrogen heterocycles including iminosugars [J].
Cooper, TS ;
Larigo, AS ;
Laurent, P ;
Moody, CJ ;
Takle, AK .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (07) :1252-1262